EP0023260B1 - Hydrate de 5-amino-benzimidazol-2-one, procédé pour sa préparation et son utilisation comme précurseur pour colorants - Google Patents

Hydrate de 5-amino-benzimidazol-2-one, procédé pour sa préparation et son utilisation comme précurseur pour colorants Download PDF

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Publication number
EP0023260B1
EP0023260B1 EP80103381A EP80103381A EP0023260B1 EP 0023260 B1 EP0023260 B1 EP 0023260B1 EP 80103381 A EP80103381 A EP 80103381A EP 80103381 A EP80103381 A EP 80103381A EP 0023260 B1 EP0023260 B1 EP 0023260B1
Authority
EP
European Patent Office
Prior art keywords
amino
benzimidazol
hydrate
benzimidazolone
acidification
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired
Application number
EP80103381A
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German (de)
English (en)
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EP0023260A1 (fr
Inventor
Otto Dr. Arndt
Rainer Lemberg
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Hoechst AG
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Hoechst AG
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Filing date
Publication date
Application filed by Hoechst AG filed Critical Hoechst AG
Publication of EP0023260A1 publication Critical patent/EP0023260A1/fr
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Publication of EP0023260B1 publication Critical patent/EP0023260B1/fr
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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
    • C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
    • C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
    • C07D235/24—Benzimidazoles; Hydrogenated benzimidazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached in position 2
    • C07D235/26—Oxygen atoms
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B29/00—Monoazo dyes prepared by diazotising and coupling
    • C09B29/0025—Monoazo dyes prepared by diazotising and coupling from diazotized amino heterocyclic compounds
    • C09B29/0029—Monoazo dyes prepared by diazotising and coupling from diazotized amino heterocyclic compounds the heterocyclic ring containing only nitrogen as heteroatom
    • C09B29/0037—Monoazo dyes prepared by diazotising and coupling from diazotized amino heterocyclic compounds the heterocyclic ring containing only nitrogen as heteroatom containing a five-membered heterocyclic ring with two nitrogen atoms

Definitions

  • 5-Amino-benzimidazolone- (2) can be used as a diazo component and as an N-acetoacetyl compound as a coupling component for azo compounds, in particular azo pigments.
  • the reduction product is unstable and is rapidly oxidized in air, so that the amine is not isolated, but is used directly in the form of the mixture obtained with ammonium chloride for diazotization.
  • the invention thus relates to 5-amino-benzimidazol-2-one monohydrate and to a process for its preparation and its use as an intermediate dye product.
  • the 5-amino-benzimidazol-2-one monohydrate according to the invention is prepared by catalytic reduction of 5-nitro-benzimidazolone- (2) and is characterized in that the reduction is carried out as a catalytic hydrogenation in an aqueous medium and in the presence of a base , which releases 5-amino-benzimidazolone- (2) by adding acid from the solution of its salt and isolating the crystallized hydrate.
  • Suitable bases are those compounds which are capable of salt formation with the 5-nitro- and 5-aminobenzimidazolone- (2), preferably inorganic bases, such as aqueous ammonia, alkali metal hydroxides or salts of strong bases with weak acids, which are present in aqueous solution by hydrolysis, such as sodium carbonate, disodium phosphate or borax.
  • inorganic bases such as aqueous ammonia, alkali metal hydroxides or salts of strong bases with weak acids, which are present in aqueous solution by hydrolysis, such as sodium carbonate, disodium phosphate or borax.
  • alkali hydroxides especially sodium hydroxide, are used.
  • Suitable acids are in principle all acidic compounds which are capable of releasing the amine from the aminobenzimidazolone salt obtained.
  • carbon dioxide comes into question, but preferably strong mineral acids, such as sulfuric acid, nitric acid and in particular hydrochloric acid.
  • the catalytic hydrogenation takes place under customary conditions. Since the alkaline medium is used, in addition to precious metal catalysts such as platinum or palladium, cheap nickel catalysts can also be used. Since the product should go and stay in solution, the appropriate temperature depends on the amount of water and the type and amount of base added.
  • Is preferably carried out in a temperature range of 50 to 200 ° C, in particular 80 to 150 ° C.
  • the hydrogen pressure is preferably in the range from about 5 to 150 bar, in particular from 20 to 100 bar.
  • the acid is preferably added after the catalyst has been separated off, especially when an acid-sensitive hydrogenation catalyst such as nickel is used.
  • the amount of base is generally one equivalent, based on the 5-nitro-benzimidazo ion, the preferred procedure being that the catalytic reduction is carried out in the presence of about 1/2 equivalents of the base and only after the reduction is the one formed 5-aminobenzimidazolone (2) is completely converted into the salt by adding another half equivalent of base.
  • the acid is expediently added at a temperature at which the 5-amino-benzimidazolone (2) is present in solution, that is to say preferably at an elevated temperature, in particular at about 60-100 ° C.
  • the acid is expediently dimensioned such that the reaction mixture reacts neutrally. An excess of acid generally has no advantages and only pollutes the wastewater.
  • reaction mixture is expediently allowed to cool slowly, the hydrate being obtained in coarsely crystalline, easily filterable form.
  • a drying temperature of 60 ° C. is expediently not exceeded.
  • a particularly expedient manufacturing process thus consists of the following steps: An aqueous suspension of 5-nitro-benzimi dazolon- (2) is mixed in a hydrogenation autoclave at about 80 ° C. with a nickel contact and V2 equivalent of 33% by weight sodium hydroxide solution. The hydrogenation then takes place under customary conditions until the hydrogen uptake has ended. The still hot reduction mixture is mixed with a further 1/2 equivalent of 33% by weight sodium hydroxide solution and stirred briefly. The reaction mixture is filtered at about 70-100 ° C., preferably 85 ° C., in about 1 equivalent of warm, 30% by weight hydrochloric acid. If necessary, the pH is adjusted to 6.5-7.0 and the mixture is slowly cooled. The 5-amino-benzimidazol-2-one monohydrate crystallizes in the form of coarse needles. It is filtered off and dried at 60 ° C. in a stream of nitrogen. The product is only slightly sensitive to oxidation in air.
  • Example 2 is carried out like Example 1 with the difference that before the cat. Reduction 600 parts of 33% sodium hydroxide solution can be added at 95 ° C. There is no addition of sodium hydroxide solution after the reduction.
  • example 3 corresponds to example 1, but with the difference that the subsequent addition of 300 parts of 33% sodium hydroxide solution is omitted and instead 4000 parts of water are added to completely dissolve the 5-amino-benzimidazolone.
  • the suspension of the 5-amino-benzimidazolone (2) hydrate formed is much more difficult to filter than the product according to Example 1.
  • the bulk density is 400-500 g / l, while the bulk weight of the crystals of Example 1 is 600-800 g / I is.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Claims (8)

1. Monohydrate d'amino-5-benzimidazolone-2.
2. Procédé de péparation du monohydrate d'amino-5-benzimidazolone-2, procédé caractérisé en ce qu'on hydrogène catalytiquement la nitro-5-benzimidazolone-2 en milieu aqueux et en présence d'une base capable de former un sel avec la nitro-5 benzimidazolone-2, on libère l'amino-5-benzimidazolone-2 de la solution de son sel par addition d'un acide et on isole l'hydrate qui a cristallisé.
3. Procédé selon la revendication 2, caractérisé en ce que la base est un hydroxyde de métal alcalin.
4. Procédé selon l'une des revendications 2 et 3, caractérisé en ce que l'acide est l'acide chlorhydrique.
5. Procédé selon l'une quelconque des revendications 2 à 4, caractérisé en ce qu'on ajoute l'acide après avoir séparé le catalyseur d'hydrogénation.
6. Procédé selon l'une quelconque des revendications 2 à 5, caractérisé en ce qu'on ajoute l'acide à une température de 60 à 100 °C.
7. Procédé selon l'une quelconque des revendications 2 à 6, caractérisé en ce qu'on refroidit le mélange réactionnel, après l'addition d'acide, pour isoler l'hydrate.
8. Application du monohydrate d'amino-5-benzimidazolone-2 comme précurseur de colorants.
EP80103381A 1979-06-25 1980-06-18 Hydrate de 5-amino-benzimidazol-2-one, procédé pour sa préparation et son utilisation comme précurseur pour colorants Expired EP0023260B1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE2925541 1979-06-25
DE19792925541 DE2925541A1 (de) 1979-06-25 1979-06-25 5-amino-benzimidazol-2-on-hydrat, verfahren zu seiner herstellung und seine verwendung als farbenvorprodukt

Publications (2)

Publication Number Publication Date
EP0023260A1 EP0023260A1 (fr) 1981-02-04
EP0023260B1 true EP0023260B1 (fr) 1983-01-12

Family

ID=6074071

Family Applications (1)

Application Number Title Priority Date Filing Date
EP80103381A Expired EP0023260B1 (fr) 1979-06-25 1980-06-18 Hydrate de 5-amino-benzimidazol-2-one, procédé pour sa préparation et son utilisation comme précurseur pour colorants

Country Status (3)

Country Link
EP (1) EP0023260B1 (fr)
JP (1) JPS567769A (fr)
DE (2) DE2925541A1 (fr)

Families Citing this family (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE19747175A1 (de) 1997-10-24 1999-04-29 Clariant Int Ltd Chlorhaltige Triphendioxazin-Verbindungen
US6617453B1 (en) 1997-10-24 2003-09-09 Clariant Finance (Bvi) Limited Triphendioxazine compounds
DE19913401A1 (de) 1999-03-25 2000-09-28 Clariant Gmbh Verfahren zur Herstellung von Dioxazin-Verbindungen
US20160136077A1 (en) * 2013-06-21 2016-05-19 L'oreal Oxidation dyeing process using a composition comprising an aminobenzimidazolone oxidation base and a metal catalyst
FR3007277B1 (fr) * 2013-06-21 2015-06-19 Oreal Procede de coloration d'oxydation mettant en œuvre une composition comprenant une base d'oxydation aminobenzimidazolone et un catalyseur metallique

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CH597316A5 (fr) * 1975-02-21 1978-03-31 Ciba Geigy Ag

Also Published As

Publication number Publication date
JPS567769A (en) 1981-01-27
EP0023260A1 (fr) 1981-02-04
DE2925541A1 (de) 1981-01-22
DE3061609D1 (en) 1983-02-17
JPS6328910B2 (fr) 1988-06-10

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